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Novel heterogeneous ruthenium racemization catalyst for dynamic kinetic resolution of chiral aliphatic amines

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Abstract

Only few dynamic kinetic resolution (DKR) systems are known for chiral aliphatic amines due to the difficult racemization of these amines. In this work, each aspect of the DKR of aliphatic amines is investigated. Various ruthenium catalysts were evaluated to increase their applicability in racemization as an alternative to established heterogeneous palladium catalysts. A heterogeneous Ru(III) on zeolite catalyst showed good activity for racemization in aprotic polar media. Next, kinetic resolution was evaluated; excellent yields (50%) and selectivities (>99%) were obtained in apolar solvents when employing isopentyl propionate as resolving agent. After evaluation of both components, the complete dynamic kinetic resolution of an aliphatic amine was established with good selectivity (97%), enantiomeric excess (96%) and a yield exceeding the kinetic resolution limit of 50%.

Graphical abstract: Novel heterogeneous ruthenium racemization catalyst for dynamic kinetic resolution of chiral aliphatic amines

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Publication details

The article was received on 26 Jul 2019, accepted on 18 Nov 2019 and first published on 21 Nov 2019


Article type: Paper
DOI: 10.1039/C9GC02615K
Green Chem., 2019, Advance Article

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    Novel heterogeneous ruthenium racemization catalyst for dynamic kinetic resolution of chiral aliphatic amines

    K. Adriaensen, J. Vercammen, C. Van Goethem, S. Eyley, I. Vankelecom, W. Thielemans and D. De Vos, Green Chem., 2019, Advance Article , DOI: 10.1039/C9GC02615K

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